Title: 20 Best B&B in Winchester, VA - Bed and Breakfast from $158 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx6056879)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.com/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d6056879.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=6056879&startDate=2026-05-15&endDate=2026-05-17&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "excellent" [](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/d7802d8b_y.jpg) ### Hilton Garden Inn Dulles North 8/10 Good "Good goodbye " [](https://expedia.com/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information) ![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346_y.jpg) ### Sleep Inn & Suites Winchester near University 10/10 Excellent "Yes the kitchen was a blessing " [](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "Staff were very nice. Clean room and diningroom. Easy on & off Rt 81\. in Winchester. 1 1/2 hr to the car train in Lorton Va. Great way to eliminate crazy traffic on Rt 95 to go Rt66 off Rt 81\. " [](https://expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 8/10 Good "Very nice and conveniently located" [](https://expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Best Western Leesburg Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/12700/12669/bcd21d29_y.jpg) ### Best Western Leesburg Hotel & Conference Center 10/10 Excellent "Friendly staff, clean room and good breakfast." [](https://expedia.com/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information) ![Mimslyn Inn Historic Hotels Of America](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/5175eb5d_y.jpg) ### Mimslyn Inn Historic Hotels Of America 10/10 Excellent "The hotel is in a nice location. Close the Luray cavern and walkable in the Luray town. Clean and spacious room. Friendly staff. " [](https://expedia.com/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.Hotel-Information) ![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a_y.jpg) ### SpringHill Suites by Marriott Winchester 10/10 Excellent "SpringHill Suites is my go-to hotel in the Winchester area. " [](https://expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Quality Inn Harpers Ferry - Charles Town](https://images.trvl-media.com/lodging/1000000/30000/25200/25179/e301290f_y.jpg) ### Quality Inn Harpers Ferry - Charles Town 10/10 Excellent "Clean room in good shape, temperature great, close to park, breakfast very good. All staff very pleasant!" [](https://expedia.com/Martinsburg-Hotels-Quality-Inn.h25179.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 1,963 | | ----------------- | ------ | | Accommodation | 34 B&B | | Lowest Price | $158 | | Highest Price | $523 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in Winchester? ### When is the best time to book a Bed and Breakfast in Winchester? > September often sees a delightful mix of warm days and cool evenings, making it ideal for leisurely strolls through local parks or visiting historical sites. The community also hosts several festivals celebrating the harvest, offering visitors a taste of local culture and cuisine. > > > For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month provides a unique opportunity to explore Winchester's attractions without the crowds, and you can enjoy the area's natural beauty as the landscape transitions into winter. ### What is the difference between a Winchester Bed & Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Historic-Hotel.0-n6164092-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Restaurants in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Restaurants.0-n6164092-0-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - [Casino Hotels in Old Town Winchester ](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels-Casino-Hotel.0-n6164092-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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[Hotels near Old Court House Civil War Museum ](https://www.expedia.com/Old-Court-House-Civil-War-Museum-Hotels.0-l553248621532661844-0.Travel-Guide-Filter-Hotels) - [Frederick County Hotels ](https://www.expedia.com/Destinations-In-Frederick-County.d553248635976431672.Hotel-Destinations) - [Hotels near Shenandoah Valley Discovery Museum ](https://www.expedia.com/Shenandoah-Valley-Discovery-Museum-Hotels.0-l553248621587527659-0.Travel-Guide-Filter-Hotels) - [Hotels near George Washington's Office ](https://www.expedia.com/George-Washingtons-Office-Hotels.0-l6164042-0.Travel-Guide-Filter-Hotels) - [Hotels near Handley Regional Library ](https://www.expedia.com/Handley-Regional-Library-Hotels.0-l6164024-0.Travel-Guide-Filter-Hotels) - [Hotels near Mt Hebron Cemetery ](https://www.expedia.com/Mt-Hebron-Cemetery-Hotels.0-l553248621532661845-0.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Little Theater ](https://www.expedia.com/Winchester-Little-Theater-Hotels.0-l6164047-0.Travel-Guide-Filter-Hotels) - [Hotels near Stonewall Jackson's Headquarters ](https://www.expedia.com/Stonewall-Jacksons-Headquarters-Hotels.0-l6164032-0.Travel-Guide-Filter-Hotels) - [Hotels near Patsy Cline Historic House ](https://www.expedia.com/Patsy-Cline-Historic-House-Hotels.0-l553248621532661841-0.Travel-Guide-Filter-Hotels) - [Hotels near Museum of the Shenandoah Valley ](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Hotels.0-l6127313-0.Travel-Guide-Filter-Hotels) - [Hotels near Jim Barnett Park ](https://www.expedia.com/Jim-Barnett-Park-Hotels.0-l6164028-0.Travel-Guide-Filter-Hotels) - [Hotels near Abram's Delight ](https://www.expedia.com/Abrams-Delight-Hotels.0-l553248621532661839-0.Travel-Guide-Filter-Hotels) - [Hotels near Winchester-Frederick County Convention & Visitors Bureau ](https://www.expedia.com/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels) - [Hotels near Shenandoah University ](https://www.expedia.com/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall ](https://www.expedia.com/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Hotels near ValleyHealth Winchester Medical Center ](https://www.expedia.com/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) - [Hotels near Rock Harbor Golf Course ](https://www.expedia.com/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels) - [Flights from Frederick County ](https://www.expedia.com/lp/flights/553248635976431672/flights-from-frederick-county) - [Flights to Frederick County ](https://www.expedia.com/Destinations-In-Frederick-County.d553248635976431672.Flight-Destinations) - [Flights from Winchester Regional ](https://www.expedia.com/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Richmond (RIC) to Winchester (WGO) ](https://www.expedia.com/lp/flights/ric/wgo/richmond-to-winchester) - [Flights from Houston (IAH) to Winchester (WGO) ](https://www.expedia.com/lp/flights/iah/wgo/houston-to-winchester) - [Flights from Washington (IAD) to Winchester (WGO) ](https://www.expedia.com/lp/flights/iad/wgo/washington-to-winchester) - [Flights from Baltimore (BWI) to Winchester (WGO) ](https://www.expedia.com/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Pittsburgh (PIT) to Winchester (WGO) ](https://www.expedia.com/lp/flights/pit/wgo/pittsburgh-to-winchester) - [Flights from Washington (DCA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/dca/wgo/washington-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO) ](https://www.expedia.com/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from Charlotte (CLT) to Winchester (WGO) ](https://www.expedia.com/lp/flights/clt/wgo/charlotte-to-winchester) - [Flights from New York (JFK) to Winchester (WGO) ](https://www.expedia.com/lp/flights/jfk/wgo/new-york-to-winchester) - [Flights from Norfolk (ORF) to Winchester (WGO) ](https://www.expedia.com/lp/flights/orf/wgo/norfolk-to-winchester) - [Flights from Raleigh (RDU) to Winchester (WGO) ](https://www.expedia.com/lp/flights/rdu/wgo/raleigh-to-winchester) - [Flights from Knoxville (TYS) to Winchester (WGO) ](https://www.expedia.com/lp/flights/tys/wgo/knoxville-to-winchester) - [Flights from Chattanooga (CHA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/cha/wgo/chattanooga-to-winchester) - [Flights from Atlanta (ATL) to Winchester (WGO) ](https://www.expedia.com/lp/flights/atl/wgo/atlanta-to-winchester) - [Flights from Philadelphia (PHL) to Winchester (WGO) ](https://www.expedia.com/lp/flights/phl/wgo/philadelphia-to-winchester) - [Flights from Chicago (ORD) to Winchester (WGO) ](https://www.expedia.com/lp/flights/ord/wgo/chicago-to-winchester) - [Flights from Seattle (SEA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/sea/wgo/seattle-to-winchester) - [Flights from Boston (BOS) to Winchester (WGO) ](https://www.expedia.com/lp/flights/bos/wgo/boston-to-winchester) - [Flights from Nashville (BNA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/bna/wgo/nashville-to-winchester) - [Flights from Orlando (MCO) to Winchester (WGO) ](https://www.expedia.com/lp/flights/mco/wgo/orlando-to-winchester) - [Flights from Greensboro (GSO) to Winchester (WGO) ](https://www.expedia.com/lp/flights/gso/wgo/greensboro-to-winchester) - [Flights from Columbus (CMH) to Winchester (WGO) ](https://www.expedia.com/lp/flights/cmh/wgo/columbus-to-winchester) - [Flights from Indianapolis (IND) to Winchester (WGO) ](https://www.expedia.com/lp/flights/ind/wgo/indianapolis-to-winchester) - [Flights from St. Louis (STL) to Winchester (WGO) ](https://www.expedia.com/lp/flights/stl/wgo/st-louis-to-winchester) - [Flights from Los Angeles (LAX) to Winchester (WGO) ](https://www.expedia.com/lp/flights/lax/wgo/los-angeles-to-winchester) - [Flights from Savannah (SAV) to Winchester (WGO) ](https://www.expedia.com/lp/flights/sav/wgo/savannah-to-winchester) - [Flights from San Diego (SAN) to Winchester (WGO) ](https://www.expedia.com/lp/flights/san/wgo/san-diego-to-winchester) - [Flights from Myrtle Beach (MYR) to Winchester (WGO) ](https://www.expedia.com/lp/flights/myr/wgo/myrtle-beach-to-winchester) - [Flights from Detroit (DTW) to Winchester (WGO) ](https://www.expedia.com/lp/flights/dtw/wgo/detroit-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO) ](https://www.expedia.com/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Tampa (TPA) to Winchester (WGO) ](https://www.expedia.com/lp/flights/tpa/wgo/tampa-to-winchester) - [Flights from Kansas City (MCI) to Winchester (WGO) ](https://www.expedia.com/lp/flights/mci/wgo/kansas-city-to-winchester) - [Flights to Winchester Regional ](https://www.expedia.com/Cheap-Flights-To-Winchester-Regional.d6033090.Travel-Guide-Flights) - [Flights from Minneapolis (MSP) to Winchester (WGO) ](https://www.expedia.com/lp/flights/msp/wgo/minneapolis-to-winchester) - [Flights from Cincinnati (CVG) to Winchester (WGO) ](https://www.expedia.com/lp/flights/cvg/wgo/cincinnati-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO) ](https://www.expedia.com/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Grand Rapids (GRR) to Winchester (WGO) ](https://www.expedia.com/lp/flights/grr/wgo/grand-rapids-to-winchester) - [Visit Old Town Winchester ](https://www.expedia.com/Winchester-Old-Town-Winchester.dx6164092) - [Bright Box Theater ](https://www.expedia.com/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) - [Shenandoah Valley Discovery Museum ](https://www.expedia.com/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction) - [George Washington's Office ](https://www.expedia.com/George-Washingtons-Office-Old-Town-Winchester.d6164042.Vacation-Attraction) - [Mt Hebron Cemetery ](https://www.expedia.com/Mt-Hebron-Cemetery-Winchester.d553248621532661845.Vacation-Attraction) - [Patsy Cline Historic House ](https://www.expedia.com/Patsy-Cline-Historic-House-Winchester.d553248621532661841.Vacation-Attraction) - [Museum of the Shenandoah Valley ](https://www.expedia.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) - [Jim Barnett Park ](https://www.expedia.com/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Abram's Delight ](https://www.expedia.com/Abrams-Delight-Winchester.d553248621532661839.Vacation-Attraction) - [Nalls Farm Market ](https://www.expedia.com/Nalls-Farm-Market-Winchester.d553248621532661846.Vacation-Attraction) - [Shenandoah University ](https://www.expedia.com/Shenandoah-University-Winchester.d6127311.Vacation-Attraction) - [Rock Harbor Golf Course ](https://www.expedia.com/Rock-Harbor-Golf-Course-Winchester.d553248621561864838.Vacation-Attraction) - [Car rentals near Old Town Winchester ](https://www.expedia.com/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide) - [Car rentals near Patsy Cline Historic House ](https://www.expedia.com/Car-Rentals-In-Patsy-Cline-Historic-House.d553248621532661841.Car-Rental-Guide) - [Car rentals near Nalls Farm Market ](https://www.expedia.com/Car-Rentals-In-Nalls-Farm-Market.d553248621532661846.Car-Rental-Guide) - [Car rentals near Shenandoah University ](https://www.expedia.com/Car-Rentals-In-Shenandoah-University.d6127311.Car-Rental-Guide) - [Van Car Rentals near Shenandoah University ](https://www.expedia.com/Van-Car-Rentals-In-Shenandoah-University.d6127311-tVan.Car-Rental-Guide-Class) - [Car rentals near Apple Blossom Mall ](https://www.expedia.com/Car-Rentals-In-Apple-Blossom-Mall.d6164018.Car-Rental-Guide) - [Car rentals near ValleyHealth Winchester Medical Center ](https://www.expedia.com/Car-Rentals-In-Winchester-Medical-Center.d6164057.Car-Rental-Guide) - [Car rentals near College Park ](https://www.expedia.com/Car-Rentals-In-College-Park.d553248635975870482.Car-Rental-Guide) - [Car rental Winchester Airport (WGO) ](https://www.expedia.com/Car-Rentals-In-Winchester-Regional.d6033090.Car-Rental-Guide)